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Zoledronate Disodium

PubChem CID
23649597
Structure
Zoledronate Disodium_small.png
Zoledronate Disodium_3D_Structure.png
Molecular Formula
Synonyms
  • Zoledronate disodium hydrate
  • Zoledronate disodium tetrahydrate
  • 165800-07-7
  • Zoledronate disodium
  • Zoledronate disodium [USAN]
Molecular Weight
388.11 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2008-01-22
  • Modify:
    2025-01-11
Description
Zoledronate Disodium is the disodium salt form of zoledronate, a synthetic imidazole, third generation bisphosphonate analog of pyrophosphate with antiresorptive activity. Zoledronate binds to hydroxyapatite crystals in the bone matrix and inhibits farnesyl pyrophosphate (diphosphate) synthase, thereby preventing protein prenylation within the mevalonate pathway. This leads to the loss of downstream metabolites essential for osteoclast function, leading to the induction of apoptosis and eventually, osteoclast-cell death. By preventing osteoclast-mediated bone resorption, zoledronate decreases bone turnover and stabilizes the bone matrix.
An imidobisphosphonate inhibitor of BONE RESORPTION that is used for the treatment of malignancy-related HYPERCALCEMIA; OSTEITIS DEFORMANS; and OSTEOPOROSIS.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Zoledronate Disodium.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

disodium;hydroxy-[1-hydroxy-1-[hydroxy(oxido)phosphoryl]-2-imidazol-1-ylethyl]phosphinate;tetrahydrate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C5H10N2O7P2.2Na.4H2O/c8-5(15(9,10)11,16(12,13)14)3-7-2-1-6-4-7;;;;;;/h1-2,4,8H,3H2,(H2,9,10,11)(H2,12,13,14);;;4*1H2/q;2*+1;;;;/p-2
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

IEJZOPBVBXAOBH-UHFFFAOYSA-L
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1=CN(C=N1)CC(O)(P(=O)(O)[O-])P(=O)(O)[O-].O.O.O.O.[Na+].[Na+]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C5H16N2Na2O11P2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

165800-07-7

2.3.2 UNII

2.3.3 ChEMBL ID

2.3.4 KEGG ID

2.3.5 NCI Thesaurus Code

2.3.6 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 2-(imidazol-1-yl)-1-hydroxyethylidene-1,1-bisphosphonic acid
  • CGP 42'446
  • CGP 42446
  • CGP 42446A
  • CGP-42'446
  • CGP-42446
  • CGP42'446
  • CGP42446
  • zoledronate
  • zoledronic acid
  • zoledronic acid anhydrous
  • Zometa

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
388.11 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
12
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
388.00247189 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
388.00247189 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
163 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
22
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
322
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
7
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Chemical Classes

3.2.1 Drugs

3.2.1.1 Human Drugs
Breast Feeding; Lactation; Bisphosphonates; Bone Density Conservation Agents; Diphosphonates;

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug Classes

Breast Feeding; Lactation; Bisphosphonates; Bone Density Conservation Agents; Diphosphonates;

6.2 Clinical Trials

6.2.1 EU Clinical Trials Register

7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

Bone Density Conservation Agents
Agents that inhibit BONE RESORPTION and/or favor BONE MINERALIZATION and BONE REGENERATION. They are used to heal BONE FRACTURES and to treat METABOLIC BONE DISEASES such as OSTEOPOROSIS. (See all compounds classified as Bone Density Conservation Agents.)

8 Toxicity

8.1 Toxicological Information

8.1.1 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Because no information is available on the use of zoledronic acid during breastfeeding, an alternate drug may be preferred, especially while nursing a newborn or preterm infant. However, absorption of zoledronic acid by a breastfed infant is unlikely.

◉ Effects in Breastfed Infants

Relevant published information was not found as of the revision date.

◉ Effects on Lactation and Breastmilk

Relevant published information was not found as of the revision date.

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Chemical Co-Occurrences in Literature

9.4 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 WIPO PATENTSCOPE

10.3 Chemical Co-Occurrences in Patents

10.4 Chemical-Disease Co-Occurrences in Patents

11 Classification

11.1 MeSH Tree

11.2 NCI Thesaurus Tree

11.3 KEGG: ATC

11.4 KEGG: Target-based Classification of Drugs

11.5 KEGG: Drug Groups

11.6 ChemIDplus

11.7 MolGenie Organic Chemistry Ontology

12 Information Sources

  1. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  4. Drugs and Lactation Database (LactMed)
  5. EU Clinical Trials Register
  6. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
    Target-based classification of drugs
    http://www.genome.jp/kegg-bin/get_htext?br08310.keg
  7. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  8. Wikidata
    zoledronate disodium tetrahydrate
    https://www.wikidata.org/wiki/Q27268106
  9. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    Bone Density Conservation Agents
    https://www.ncbi.nlm.nih.gov/mesh/68050071
  10. PubChem
  11. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  12. PATENTSCOPE (WIPO)
CONTENTS